Determination of the absolute stereochemical configuration of chiral centers is a critical step in the synthesis of complex natural products. While not as prevalent in natural products, chiral epoxides are important intermediates in the synthesis of a large number of complex molecules. Unfortunately, there is a lack of practical analytical methods for assigning the absolute configuration of chiral epoxides. Our lab has developed the competing enantioselective conversion (CEC) method to determine the absolute configuration of chiral alcohols, amines, oxazolidinones, and lactams. This approach uses kinetic resolution reagents to establish absolute configuration based on targeted reactivity. An expoxide of “unknown” stereochemistry is reacted with both enantiomers of the kinetic resolution agent. The fastest-reacting enantiomer is identified, and comparison with an established mnemonic allows for the configuration of the original unknown epoxide to be determined. Our method works for both cyclic and acyclic epoxides.

Determining absolute configuration of chiral epoxides using the competing enantioselective conversion method

251st National Meeting (2016)

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